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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2693.
Published online 2010 September 30. doi:  10.1107/S1600536810038523
PMCID: PMC2983207

11-{[2-(3-Fluoro­phen­yl)eth­yl](meth­yl)amino}­penta­cyclo­[5.4.0.02,6.03,10.05,9]undecan-8-one

Abstract

In the title compound, C20H22FNO, the distances close to the carbonyl and amine are: N—O = 3.232 (4) Å and N—C = 2.666 (5) Å. The crystal packing is unremarkable.

Related literature

For in vitro σ-receptor affinity of tris­homocubane derivatives related to the title compound, see: Nguyen et al. (1996 [triangle]); Liu et al. (1999 [triangle]). For in vivo pharmacology of related tris­homocubanes, see: Liu et al. (2001 [triangle], 2007 [triangle]). For rationalization of observed structure–affinity relationships of tris­homocubanes at σ-receptors using mol­ecular modeling, see: Banister et al. (2010 [triangle]). For X-ray crystallographic studies of biologically active tris­homocubanes related to the title compound, see: Hambley et al. (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2693-scheme1.jpg

Experimental

Crystal data

  • C20H22FNO
  • M r = 311.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2693-efi1.jpg
  • a = 10.5450 (18) Å
  • b = 10.980 (2) Å
  • c = 13.822 (3) Å
  • β = 95.214 (8)°
  • V = 1593.8 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 150 K
  • 0.25 × 0.20 × 0.15 mm

Data collection

  • Bruker–Nonius APEXII FR591 diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1999 [triangle]) T min = 0.684, T max = 0.746
  • 17270 measured reflections
  • 2773 independent reflections
  • 1566 reflections with I > 2σ(I)
  • R int = 0.087

Refinement

  • R[F 2 > 2σ(F 2)] = 0.087
  • wR(F 2) = 0.271
  • S = 1.14
  • 2773 reflections
  • 209 parameters
  • H-atom parameters constrained
  • Δρmax = 0.69 e Å−3
  • Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker–Nonius, 2003 [triangle]); cell refinement: SAINT (Bruker–Nonius, 2003); data reduction: SAINT and XPREP (Bruker–Nonius, 2003 [triangle]); program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]), WinGX (Farrugia, 1999 [triangle]) and POV-RAY (Cason, 2002 [triangle]); software used to prepare material for publication: enCIFer (Allen et al., 2004 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038523/rk2233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038523/rk2233Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We gratefully acknowledge the Australian Research Council for support. JKC acknowledges the Marie Curie IIF scheme of the 7th EU Framework Program.

supplementary crystallographic information

Comment

Trishomocubanes have been shown to have in vitroσ-receptor affinity and selectivity [Nguyen et al., (1996); Liu et al., (1999)] and a number of their crystal structures have been reported [Hambley et al., (2000)]. Several trishomocubane derivatives synthesized in our laboratory were reported to possess anti-cocaine activity in vivo [Liu et al., (2001), (Liu et al., (2007)]. The importance of the nature ofthe hemiaminal bridge of N-(2-(3-fluorophenyl)ethyl)-4-azahexacyclo [5.4.1.02,6.03,10.05,9.08,11]dodecan-3-ol I *(Fig. 1) to σ-receptor binding was demonstrated by the reduced affinity, and off-target activity, of the corresponding hemiaminal ether, N-(2-(3-fluorophenyl)ethyl)-3-amino-4-oxapentacyclo [5.4.1.02,6.03,10.05,9.08,11]dodecane II [Banister et al., (2010)] (Fig. 1). In our ongoing efforts to elucidate the nature of σ-receptor binding we have synthesized the title compound III (Fig. 1) as a methyl homologue of I, representing a "locked" form of the non-transannular, aminoketone tautomer of the latter. A molecular and crystal structures were obtained to unambiguously confirm the structure of III (Fig. 2), and to identify key interatomic distances, for use in modeling studies. Important distances are those close to the carbonyl and amine, including: N1–O1 = 3.232 (4)Å; N1–C18 = 2.666 (5)Å; O1–C9 = 3.943 (5)Å; C9–C18 = 3.574 (6)Å.

Experimental

A solution of N-(2-(3-fluorophenyl)ethyl)-4-azahexacyclo [5.4.1.02,6.03,10.05,9.08,11]dodecan-3-ol (942 mg, 3.17 mmol) and 37% aqueous formaldehyde (285 µL, 3.80 mmol, 1.2 equiv.) in ClCH2CH2Cl (30 ml) was treated with NaBH(OAc)3 (3.359 g, 15.85 mmol, 5 equiv.) and the mixture stirred for 18 h. The reaction was quenched with 1 M aqueous NaOH (30 ml), and the layers separated. The aqueous layer was extracted with CH2Cl2 (3 × 15 ml) and the combined organic layers were washed with brine (25 ml), dried (Na2SO4) and the solvent evaporated. Purification was achieved using column chromatography on silica eluting with CHCl3-MeOH-conc. aq. NH4OH (90:9:1) to give N-(2-(3-fluorophenyl)ethyl)-N-methyl-11-aminopentacyclo [5.4.0.02,6.03,10.05,9]undecan-8-one III as colourless crystals (902 mg, 91%): m. pt. 363-364.5 K; Rf 0.43 (90:9:1 v/v/v CHCl3:MeOH: conc. aq. NH4OH); IR (thin film) cm-1; 2970, 2861, 1721 (C═O), 1582, 1484, 1426, 1343, 1229, 1141, 1059, 981, 939, 906, 791; 1H NMR (400 MHz, CDCl3); δ 7.25-7.19 (1H, m, ArH), 6.93 (1H, d, J = 7.9 Hz, ArH), 6.89-6.85 (2H, m, ArH), 3.02-2.97 (1H, m, CH), 2.87-2.67 (7H, m, CH), 2.66-2.62 (2H, m, CH), 2.50 (1H, t, J = 4.2 Hz, CH), 2.47-2.43 (1H, m, CH), 2.35-2.31 (1H, m, CH), 2.30 (3H, s, CH3), 1.86 (1H, d, J = 10.8 Hz, CHCH2CH), 1.48 (1H, d, J = 10.8 Hz, CHCH2CH); 13C NMR (100.6 MHz, CDCl3); δ 213.1 (C═O), 163.0 (3'-C, 1JC–F = 245.3 Hz), 143.4 (1'-C, 3JC–F = 7.4 Hz), 129.9 (5'-C, 3JC–F = 8.3 Hz), 124.5 (6'-C, 4JC–F = 2.6 Hz), 115.6 (2'-C, 2JC–F = 20.8 Hz), 112.9 (4'-C, 2JC–F = 21.1 Hz), 64.6 (CH), 57.1 (CH2), 51.6 (CH), 50.1 (CH), 46.4 (CH), 42.1 (CH), 41.6 (CH), 41.4 (CH), 40.8 (CH), 40.2 (CH), 38.5 (CH2), 37.2 (CH), 31.7 (CH2); m/z (+ESI) 312.13 ([M + H]+, 100); Anal. (C20H22NOF): calc, C 77.14, H 7.12, N 4.50; found, C 76.90, H 7.19, N 4.55. Crystals suitable for X-ray diffraction were grown by the slow evaporation of a hexane solution.

Refinement

C bound H atoms were included in idealized positions and refined using a riding-model approximation with aromatic C–H bond lengths fixed at 0.95Å and aliphatic bond lengths at 1.00Å, 0.99Å and 0.98Å for methine, methylene and methyl H atoms respectively. Uiso(H) values were fixed at 1.2Ueq of the parent C atoms, except for the methyl protons, which were fixed at 1.5Ueq(C). The highest residual peak is 0.69 eÅ-3 and is located 1.17Å from C12 with the deepest hole -0.47 eÅ-3 1.07Å from F1.

Figures

Fig. 1.
Chemical structures of I, II and III.
Fig. 2.
221ORTEP representation of III with atom numbering scheme. Displacement ellipsoids are shown at 50% probability level. H atoms are presented as a small spheres of arbitrary radius.

Crystal data

C20H22FNOF(000) = 664
Mr = 311.39Dx = 1.298 Mg m3
Monoclinic, P21/nMelting point: 363.5 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 10.5450 (18) ÅCell parameters from 2297 reflections
b = 10.980 (2) Åθ = 2.7–23.1°
c = 13.822 (3) ŵ = 0.09 mm1
β = 95.214 (8)°T = 150 K
V = 1593.8 (5) Å3Block, colourless
Z = 40.25 × 0.20 × 0.15 mm

Data collection

Bruker–Nonius APEXII FR591 diffractometer2773 independent reflections
Radiation source: rotating anode1566 reflections with I > 2σ(I)
graphiteRint = 0.087
ω and [var phi] scansθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)h = −12→12
Tmin = 0.684, Tmax = 0.746k = −13→12
17270 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.087Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.271H-atom parameters constrained
S = 1.14w = 1/[σ2(Fo2) + (0.1415P)2 + 0.2766P] where P = (Fo2 + 2Fc2)/3
2773 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.69 e Å3
0 restraintsΔρmin = −0.47 e Å3

Special details

Experimental. The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150 K under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature.
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.5938 (5)0.3609 (4)0.6172 (5)0.0588 (17)
C20.5803 (4)0.2626 (4)0.6825 (3)0.0399 (11)
H20.54500.27440.74260.048*
C30.6209 (3)0.1482 (3)0.6545 (3)0.0250 (9)
C40.6703 (4)0.1374 (4)0.5656 (3)0.0382 (11)
H40.69880.05980.54620.046*
C50.6797 (5)0.2343 (6)0.5047 (4)0.0609 (16)
H50.71230.22200.44360.073*
C60.6442 (6)0.3449 (6)0.5291 (5)0.0680 (18)
H60.65320.41200.48690.082*
C70.6123 (5)0.0379 (4)0.7189 (3)0.0503 (13)
H7A0.61560.06450.78750.060*
H7B0.6865−0.01560.71210.060*
C80.4885 (4)−0.0351 (4)0.6931 (3)0.0304 (10)
H8A0.41620.01310.71370.036*
H8B0.4758−0.04360.62160.036*
C90.5715 (4)−0.2420 (4)0.6958 (4)0.0490 (13)
H9A0.6587−0.22490.72330.074*
H9B0.5661−0.23260.62500.074*
H9C0.5486−0.32560.71190.074*
C100.4948 (4)−0.1550 (4)0.8423 (3)0.0348 (11)
H100.5795−0.12120.86750.042*
C110.3871 (4)−0.0811 (4)0.8822 (3)0.0408 (12)
H110.39560.00940.87740.049*
C120.3700 (5)−0.1303 (4)0.9854 (4)0.0506 (13)
H120.3736−0.07021.04000.061*
C130.4537 (4)−0.2406 (5)0.9980 (3)0.0502 (14)
H130.5343−0.22861.04090.060*
C140.4724 (4)−0.2781 (4)0.8898 (3)0.0479 (13)
H140.5445−0.33640.88510.057*
C150.3636 (5)−0.3402 (5)1.0322 (4)0.0542 (14)
H15A0.4011−0.42291.03280.065*
H15B0.3314−0.32161.09570.065*
C160.2635 (4)−0.3182 (5)0.9450 (3)0.0470 (13)
H160.1859−0.37050.94510.056*
C170.3392 (4)−0.3332 (4)0.8509 (4)0.0469 (13)
H170.3429−0.41860.82620.056*
C180.2639 (4)−0.2484 (4)0.7847 (3)0.0379 (11)
C190.2540 (4)−0.1331 (5)0.8456 (3)0.0429 (12)
H190.1893−0.07200.81960.052*
C200.2372 (4)−0.1834 (4)0.9485 (3)0.0435 (12)
H200.1614−0.15570.98120.052*
N10.4837 (3)−0.1570 (3)0.7364 (2)0.0259 (8)
O10.2010 (3)−0.2730 (3)0.70829 (19)0.0431 (9)
F10.5547 (4)0.4710 (3)0.6455 (4)0.128 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.035 (3)0.016 (2)0.119 (5)0.004 (2)−0.030 (3)−0.007 (3)
C20.023 (2)0.053 (3)0.043 (3)−0.007 (2)−0.0052 (18)−0.016 (2)
C30.028 (2)0.026 (2)0.020 (2)−0.0055 (18)−0.0039 (16)0.0031 (16)
C40.036 (2)0.045 (3)0.033 (3)0.001 (2)0.0019 (19)−0.007 (2)
C50.044 (3)0.104 (5)0.034 (3)−0.023 (3)−0.001 (2)0.017 (3)
C60.056 (4)0.070 (4)0.074 (4)−0.032 (3)−0.019 (3)0.038 (4)
C70.053 (3)0.047 (3)0.046 (3)−0.028 (2)−0.021 (2)0.021 (2)
C80.028 (2)0.036 (2)0.026 (2)−0.0048 (19)−0.0042 (17)0.0024 (18)
C90.039 (3)0.044 (3)0.063 (3)0.007 (2)0.001 (2)−0.011 (2)
C100.031 (2)0.041 (3)0.030 (2)−0.017 (2)−0.0098 (18)0.0099 (19)
C110.046 (3)0.050 (3)0.027 (2)−0.023 (2)0.009 (2)−0.006 (2)
C120.066 (3)0.043 (3)0.040 (3)−0.015 (3)−0.009 (2)−0.005 (2)
C130.031 (2)0.090 (4)0.028 (2)−0.011 (3)−0.0097 (19)0.012 (2)
C140.040 (3)0.044 (3)0.056 (3)−0.014 (2)−0.015 (2)0.020 (2)
C150.057 (3)0.059 (3)0.045 (3)−0.008 (3)−0.006 (2)0.018 (2)
C160.046 (3)0.070 (4)0.023 (2)−0.028 (3)−0.003 (2)0.006 (2)
C170.042 (3)0.037 (3)0.058 (3)−0.016 (2)−0.013 (2)0.010 (2)
C180.033 (2)0.051 (3)0.028 (2)−0.019 (2)−0.0031 (19)0.008 (2)
C190.039 (3)0.058 (3)0.033 (3)−0.006 (2)0.005 (2)0.001 (2)
C200.039 (3)0.060 (3)0.032 (3)−0.002 (2)0.006 (2)0.008 (2)
N10.0248 (17)0.0248 (18)0.0278 (19)−0.0006 (15)0.0002 (13)0.0012 (14)
O10.0350 (16)0.070 (2)0.0232 (16)−0.0208 (16)−0.0058 (13)0.0024 (14)
F10.088 (3)0.038 (2)0.246 (6)0.0133 (19)−0.048 (3)−0.037 (2)

Geometric parameters (Å, °)

C1—F11.347 (6)C10—H101.0000
C1—C61.384 (9)C11—C121.551 (7)
C1—C21.422 (7)C11—C191.557 (6)
C2—C31.393 (6)C11—H111.0000
C2—H20.9500C12—C131.499 (7)
C3—C41.382 (6)C12—C201.560 (7)
C3—C71.511 (6)C12—H121.0000
C4—C51.366 (7)C13—C151.551 (7)
C4—H40.9500C13—C141.581 (7)
C5—C61.323 (8)C13—H131.0000
C5—H50.9500C14—C171.579 (6)
C6—H60.9500C14—H141.0000
C7—C81.546 (6)C15—C161.546 (6)
C7—H7A0.9900C15—H15A0.9900
C7—H7B0.9900C15—H15B0.9900
C8—N11.469 (5)C16—C201.508 (7)
C8—H8A0.9900C16—C171.595 (7)
C8—H8B0.9900C16—H161.0000
C9—N11.463 (5)C17—C181.484 (6)
C9—H9A0.9800C17—H171.0000
C9—H9B0.9800C18—O11.225 (5)
C9—H9C0.9800C18—C191.529 (7)
C10—N11.458 (5)C19—C201.550 (6)
C10—C141.531 (6)C19—H191.0000
C10—C111.538 (6)C20—H201.0000
F1—C1—C6121.4 (6)C13—C12—H12117.7
F1—C1—C2116.5 (6)C11—C12—H12117.7
C6—C1—C2122.0 (5)C20—C12—H12117.7
C3—C2—C1117.2 (4)C12—C13—C15103.6 (4)
C3—C2—H2121.4C12—C13—C14102.9 (3)
C1—C2—H2121.4C15—C13—C14103.7 (4)
C4—C3—C2118.3 (4)C12—C13—H13115.0
C4—C3—C7120.2 (4)C15—C13—H13115.0
C2—C3—C7121.5 (4)C14—C13—H13115.0
C5—C4—C3122.4 (5)C10—C14—C17111.0 (3)
C5—C4—H4118.8C10—C14—C13102.3 (4)
C3—C4—H4118.8C17—C14—C13103.8 (4)
C6—C5—C4121.3 (5)C10—C14—H14113.0
C6—C5—H5119.3C17—C14—H14113.0
C4—C5—H5119.3C13—C14—H14113.0
C5—C6—C1118.7 (5)C16—C15—C1392.6 (3)
C5—C6—H6120.6C16—C15—H15A113.2
C1—C6—H6120.6C13—C15—H15A113.2
C3—C7—C8112.0 (3)C16—C15—H15B113.2
C3—C7—H7A109.2C13—C15—H15B113.2
C8—C7—H7A109.2H15A—C15—H15B110.5
C3—C7—H7B109.2C20—C16—C15104.1 (4)
C8—C7—H7B109.2C20—C16—C17103.6 (4)
H7A—C7—H7B107.9C15—C16—C17105.2 (4)
N1—C8—C7116.0 (3)C20—C16—H16114.2
N1—C8—H8A108.3C15—C16—H16114.2
C7—C8—H8A108.3C17—C16—H16114.2
N1—C8—H8B108.3C18—C17—C14112.3 (3)
C7—C8—H8B108.3C18—C17—C1699.1 (4)
H8A—C8—H8B107.4C14—C17—C16100.2 (4)
N1—C9—H9A109.5C18—C17—H17114.4
N1—C9—H9B109.5C14—C17—H17114.4
H9A—C9—H9B109.5C16—C17—H17114.4
N1—C9—H9C109.5O1—C18—C17127.6 (4)
H9A—C9—H9C109.5O1—C18—C19126.7 (4)
H9B—C9—H9C109.5C17—C18—C19103.9 (4)
N1—C10—C14114.6 (3)C18—C19—C20103.2 (4)
N1—C10—C11112.0 (3)C18—C19—C11112.2 (4)
C14—C10—C1199.4 (3)C20—C19—C1190.4 (3)
N1—C10—H10110.1C18—C19—H19115.9
C14—C10—H10110.1C20—C19—H19115.9
C11—C10—H10110.1C11—C19—H19115.9
C10—C11—C12107.3 (4)C16—C20—C19106.5 (4)
C10—C11—C19111.3 (3)C16—C20—C12102.4 (4)
C12—C11—C1989.7 (3)C19—C20—C1289.6 (3)
C10—C11—H11115.2C16—C20—H20118.0
C12—C11—H11115.2C19—C20—H20118.0
C19—C11—H11115.2C12—C20—H20118.0
C13—C12—C11105.8 (4)C10—N1—C9113.5 (3)
C13—C12—C20103.8 (4)C10—N1—C8113.1 (3)
C11—C12—C2090.3 (3)C9—N1—C8112.3 (3)
F1—C1—C2—C3−179.7 (4)C13—C14—C17—C18104.4 (4)
C6—C1—C2—C30.5 (6)C10—C14—C17—C16−109.2 (4)
C1—C2—C3—C4−0.6 (6)C13—C14—C17—C160.0 (4)
C1—C2—C3—C7179.2 (4)C20—C16—C17—C18−41.0 (4)
C2—C3—C4—C5−0.4 (6)C15—C16—C17—C18−150.0 (4)
C7—C3—C4—C5179.8 (4)C20—C16—C17—C1473.7 (4)
C3—C4—C5—C61.6 (7)C15—C16—C17—C14−35.3 (5)
C4—C5—C6—C1−1.6 (8)C14—C17—C18—O1137.7 (5)
F1—C1—C6—C5−179.2 (5)C16—C17—C18—O1−117.2 (5)
C2—C1—C6—C50.6 (8)C14—C17—C18—C19−56.7 (5)
C4—C3—C7—C8−85.8 (5)C16—C17—C18—C1948.4 (4)
C2—C3—C7—C894.4 (5)O1—C18—C19—C20127.7 (4)
C3—C7—C8—N1167.1 (4)C17—C18—C19—C20−38.0 (4)
N1—C10—C11—C12154.8 (3)O1—C18—C19—C11−136.4 (4)
C14—C10—C11—C1233.3 (4)C17—C18—C19—C1158.0 (4)
N1—C10—C11—C1958.2 (4)C10—C11—C19—C183.5 (5)
C14—C10—C11—C19−63.3 (4)C12—C11—C19—C18−105.0 (4)
C10—C11—C12—C13−7.4 (5)C10—C11—C19—C20108.1 (4)
C19—C11—C12—C13104.9 (4)C12—C11—C19—C20−0.5 (4)
C10—C11—C12—C20−111.8 (4)C15—C16—C20—C19128.1 (4)
C19—C11—C12—C200.5 (4)C17—C16—C20—C1918.3 (4)
C11—C12—C13—C15−128.9 (4)C15—C16—C20—C1234.8 (4)
C20—C12—C13—C15−34.7 (4)C17—C16—C20—C12−75.0 (4)
C11—C12—C13—C14−21.1 (4)C18—C19—C20—C1610.6 (4)
C20—C12—C13—C1473.1 (4)C11—C19—C20—C16−102.3 (4)
N1—C10—C14—C17−55.1 (5)C18—C19—C20—C12113.4 (4)
C11—C10—C14—C1764.4 (5)C11—C19—C20—C120.5 (4)
N1—C10—C14—C13−165.3 (3)C13—C12—C20—C160.0 (4)
C11—C10—C14—C13−45.8 (4)C11—C12—C20—C16106.3 (4)
C12—C13—C14—C1042.8 (4)C13—C12—C20—C19−106.8 (4)
C15—C13—C14—C10150.5 (4)C11—C12—C20—C19−0.5 (4)
C12—C13—C14—C17−72.8 (4)C14—C10—N1—C9−58.3 (5)
C15—C13—C14—C1734.9 (5)C11—C10—N1—C9−170.6 (3)
C12—C13—C15—C1653.3 (4)C14—C10—N1—C8172.2 (3)
C14—C13—C15—C16−53.9 (4)C11—C10—N1—C859.9 (4)
C13—C15—C16—C20−53.6 (4)C7—C8—N1—C1061.1 (5)
C13—C15—C16—C1755.0 (4)C7—C8—N1—C9−69.0 (5)
C10—C14—C17—C18−4.9 (6)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2233).

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